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WO1991007165A1 - Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms - Google Patents

Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms Download PDF

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Publication number
WO1991007165A1
WO1991007165A1 PCT/GB1990/001750 GB9001750W WO9107165A1 WO 1991007165 A1 WO1991007165 A1 WO 1991007165A1 GB 9001750 W GB9001750 W GB 9001750W WO 9107165 A1 WO9107165 A1 WO 9107165A1
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Prior art keywords
benzoate
aromatic
general formula
skin
organisms
Prior art date
Application number
PCT/GB1990/001750
Other languages
French (fr)
Inventor
John Adrian Betts
Original Assignee
Robertet S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Robertet S.A. filed Critical Robertet S.A.
Priority to EP90916501A priority Critical patent/EP0606197B1/en
Priority to DE69025206T priority patent/DE69025206T2/en
Priority to US07/856,955 priority patent/US5683682A/en
Publication of WO1991007165A1 publication Critical patent/WO1991007165A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations

Definitions

  • This invention relates to derivatives of aromatic benzoates as inhibitors of esterase-producing micro ⁇ organisms, for use primarily in deodorant compositions.
  • the human skin has a large natural population of micro-organisms. These organisms are nourished by various skin-secreted substances, skin cell debris, breakdown products of the skin and the organisms them ⁇ selves.
  • the skin secretions are conveniently divided into two groups, those containing water-soluble materials and constituted by eccrine and apocrine sweat, and sebum which contains lipid-soluble materials. These secretions will be referred to as 'liquid body-secretions' and they will now be described, as will their functions as they are generally understood.
  • Eccrine sweat consists mainly of a watery solution of dissolved salts and is produced by glands distributed over the whole skin surface.
  • the eccrine sweat In conditions of occlusion, e.g. feet enclosed in socks and shoes, the eccrine sweat accumulates, and ' in these warm damp conditions, the skin debris,, together with nutrients from the sweat, provide a medium for micro-organism growth with the possibility of massive overgrowth of one type. This can result, in the first instance, in odorous metabolic products, and in the second, in clinical infection with maceration of the skin and irritation.
  • Apocrine sweat is produced by the apocrine glands at specific sites on the body, notably the axillae, the anogenital area and around the nipples. Although present at birth, the apocrine glands are not functional until puberty when they are influenced by circulating, androgens. Apocrine secretion differs from eccrine sweat in containing lipids (fatty materials) and proteins. In the warm, damp occlusion met in the axillae, certain skin micro-organisms metabolise this secretion, forming free fatty acids and other breakdown products. These materials are odorous and responsible for 'body odour 1 .
  • the sebaceous glands are distributed over the skin surface except the palms and dorsae. They are most numerous on the scalp, forehead, face, back and chest.
  • the secretion, sebum consists mainly of fatty materials, wax esters, cholesterol and its esters and squalene. Normally, sebum flows freely from the glands, spreading over the skin surface.
  • the sebaceous duct through which the sebum is normally secreted becomes hyperkeratinised and the opening of the duct becomes blocked. The gland continues to produce sebum and the blocked duct distends to form a comedone.
  • the (nor ⁇ mally) commensal micro-organisms produce esterases which hydrolyse the sebum lipids, liberating free fatty acids. These fatty acids are irritant and can result in ah inflammatory reaction along the wall of the duct. Leuco ⁇ cytes invade the inflamed area and the comedone develops into a papule and then a pustule. This is a typical acne 'spot' .
  • the scalp is well supplied with sebaceous glands, and the scalp, like all skin, undergoes desquamation. Due to the presence of hair, the squames tend to be retained at the scalp surface. Sebum accumulates beneath these squames and in dandruff conditions is hydrolysed by micro-organism produced esterases to form irritant fatty acids. The irritation causes proliferation of the epidermis and increased formation of the stratum corneu which again desquamates unevenly in large clumps - the dandruff scale or flake.
  • the effect of the active ingredient is produced by the aforementioned microbial enzymes acting to split the constituents of the ester and so hydrolyse the ester back into the aromatic acid and the phenol or aromatic alcohol.
  • this action occurs almost immediately but, where skin penetration is involved, as in most dermato ⁇ logical applications, the action is progressive.
  • the above term 'anti-microbial action' means an action which inhibits microbial growth, rather than one which eliminates microbial growth completely as can be achieved by a microbicide.
  • the esterases produced by the micro-organism hydrolyse a portion of the active ingredient and, in so doing, inhibit the action of the esterase and further growth of the micro-organism.
  • the micro-organism may resume its metabolic activity and the above-mentioned process is repeated, and repetition will occur until the active ingredient is used up.
  • R represents a hydrogen or halogen atom or a C ⁇ alkyl, methoxy, ethoxy or acyloxy group
  • p is 0 or 1
  • x, y and z are each 0 or an integer of from 1 to 5, are particularly effective as inhibitors of esterase-producing micro-organisms.
  • Benzoates of the formula (I) are hydrolysed by esterases to produce three mononuclear benzene compounds which between them bear at least two hydroxyl substituents and two carboxyl substituents.
  • the hydrolysis of benzyl 4-benzoyloxybenzoate and phenyl 2-benzoyloxybenzoate are shown in Figs 1 and 2, respectively, of the accompany ⁇ ing drawings.
  • the hydrolysis products are thus highly active in performing the previously-mentioned anti ⁇ microbial and pH-lowering functions, but not to the extent of being bacteriocidal as are most conventional deodorants: not only is the elimination of cutaneous flora medically undesirable, but the use of some conven ⁇ tional deodorants has caused adverse reactions.
  • the benzoates (I) afford the further advantages of being completely odourless and non-irritant.
  • Preferred benzoates (I) are those in which p equals 0 or 1; and x, y and z are each zero. Such com ⁇ pounds have the advantage of being easy to manufacture from cheap starting materials, although the 4-benzoyloxy- benzoates are preferred from the point of view of easy purification, being solids and therefore easy to crystal ⁇ lize. Such unsubstituted benzoates (I) have the further advantage of being generally more soluble than compounds having substituted nuclei.
  • benzoates (I) is as the active ingredient in a personal deodorant composition.
  • the benzoate is first dissolved in, preferably, a perfume to form a perfume concentrate containing 5% to 50%, preferably say 10% benzoate, which is then added in an amount of about 1% to 2% to a suitable vehicle, for example ethyl alcohol, to form a deodorant composition in which the active ingredient is present in an amount of 0.1% to 0.2% and which is suitable for application by aerosol or mechanical spray.
  • a suitable vehicle for example ethyl alcohol
  • a further use of the benzoates (1) is in the treatment of dandruff and acne where decomposition of the skin fats causes irritation.
  • a skin lotion for the treatment of acne, between 0.5% and 20%, and preferably about 5%, of active ingredient is incorporated in a vehicle which may be composed of di ⁇ methyl sulphoxide, polyol, ethanol and water in suitable proportions.
  • Anti-inflammatory substances such as hydro s - cortisone or glycyrrhetic acid and healing agents such as allantoin, may also be incorporated in the end product.
  • active ingredient within the above percentages is incor ⁇ porated in a hydro-alcoholic vehicle, using solubilising agents as necessary.
  • active ingredient if liquid
  • amorphous silica powder or light magnesium carbonate which is then mixed with say 50% talcum, starch or other- suitable powder.
  • the active ingredient is solid, usually crystalline, the crystals are finely ground, for example in a micron- iser, and then mixed with say 50% talcum, starch or other suitable powder.
  • Suitable perfume compositions may also be incor ⁇ porated in the scalp/skin lotions and foot powders.
  • the skin and scalp lotions may be supplied in sprinkler bottles for application to the scalp or the affected skin area in the form of liquid droplets which are massaged into the scalp/skin.
  • the lotion may be applied by means of a pad or compress which is pre-impregnated and supplied in a sealed package ' ; the pad is partially exposed and then applied to an affected skin area, at least once per day.
  • the inhibitors for use in treating the scalp or skin may comprise ointments, gels, creams, lotions , sprays or powders .
  • the inhibitors for foot treatment are preferably in powder form, as indicated above, but might also be supplied as liquids or in sprays etc.
  • the reaction scheme may be represented as follows:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cosmetics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Inhibitors of esterase-producing microorganisms comprise, as acitve ingredient, a benzyl or phenyl benzoyloxybenzoate (I) which is hydrolysed by esterases to produce three mononuclear benzene compounds which between them bear at least two hydroxyl and two carboxyl substances, and which impart an anti-microbial action. The inhibitors may be formulated as personal deodorants or dermatological agents.

Description

DERIVATIVES OF AROMATIC BENZOATES AS INHIBITORS OF ESTERASE-PRODUCING MICRO-ORGANISMS
This invention relates to derivatives of aromatic benzoates as inhibitors of esterase-producing micro¬ organisms, for use primarily in deodorant compositions.
The human skin has a large natural population of micro-organisms. These organisms are nourished by various skin-secreted substances, skin cell debris, breakdown products of the skin and the organisms them¬ selves. The skin secretions are conveniently divided into two groups, those containing water-soluble materials and constituted by eccrine and apocrine sweat, and sebum which contains lipid-soluble materials. These secretions will be referred to as 'liquid body-secretions' and they will now be described, as will their functions as they are generally understood.
Eccrine sweat consists mainly of a watery solution of dissolved salts and is produced by glands distributed over the whole skin surface. In conditions of occlusion, e.g. feet enclosed in socks and shoes, the eccrine sweat accumulates, and ' in these warm damp conditions, the skin debris,, together with nutrients from the sweat, provide a medium for micro-organism growth with the possibility of massive overgrowth of one type. This can result, in the first instance, in odorous metabolic products, and in the second, in clinical infection with maceration of the skin and irritation.
Apocrine sweat is produced by the apocrine glands at specific sites on the body, notably the axillae, the anogenital area and around the nipples. Although present at birth, the apocrine glands are not functional until puberty when they are influenced by circulating, androgens. Apocrine secretion differs from eccrine sweat in containing lipids (fatty materials) and proteins. In the warm, damp occlusion met in the axillae, certain skin micro-organisms metabolise this secretion, forming free fatty acids and other breakdown products. These materials are odorous and responsible for 'body odour1.
The sebaceous glands are distributed over the skin surface except the palms and dorsae. They are most numerous on the scalp, forehead, face, back and chest. The secretion, sebum, consists mainly of fatty materials, wax esters, cholesterol and its esters and squalene. Normally, sebum flows freely from the glands, spreading over the skin surface. In acneic and certain other skin conditions, the sebaceous duct through which the sebum is normally secreted becomes hyperkeratinised and the opening of the duct becomes blocked. The gland continues to produce sebum and the blocked duct distends to form a comedone. Also blocked in the duct, the (nor¬ mally) commensal micro-organisms produce esterases which hydrolyse the sebum lipids, liberating free fatty acids. These fatty acids are irritant and can result in ah inflammatory reaction along the wall of the duct. Leuco¬ cytes invade the inflamed area and the comedone develops into a papule and then a pustule. This is a typical acne 'spot' .
The scalp is well supplied with sebaceous glands, and the scalp, like all skin, undergoes desquamation. Due to the presence of hair, the squames tend to be retained at the scalp surface. Sebum accumulates beneath these squames and in dandruff conditions is hydrolysed by micro-organism produced esterases to form irritant fatty acids. The irritation causes proliferation of the epidermis and increased formation of the stratum corneu which again desquamates unevenly in large clumps - the dandruff scale or flake.
In our International Application No. PCT/GB37/ 00323 (Publication No. W087/06827) we disclosed an in¬ hibitor of esterase-producing microorganisms in which the active ingredient comprised an aromatic acid ester of a phenol or of an aromatic alcohol, the phenol or aromatic alcohol being sufficiently water-soluble to impart an anti-microbial action and the aromatic acid being sufficiently water-soluble to impart an anti¬ microbial action and/or to lower the pH of liquid body- secretion to a level which at least inhibits the growth of micro-organisms in the liquid body-secretions; for use in deodorants the active ingredient may be incorpor¬ ated in a perfume composition which is then incorporated in a vehicle such as ethanol; for use in a dermatological composition, the active ingredient may be incorporated in an acceptable vehicle containing for example, a polyol or dimethyl suphoxide which may also act as a skin pene- trant.
The effect of the active ingredient is produced by the aforementioned microbial enzymes acting to split the constituents of the ester and so hydrolyse the ester back into the aromatic acid and the phenol or aromatic alcohol. On a skin surface, such as in deodorant appli¬ cations, this action occurs almost immediately but, where skin penetration is involved, as in most dermato¬ logical applications, the action is progressive.
The above term 'anti-microbial action' means an action which inhibits microbial growth, rather than one which eliminates microbial growth completely as can be achieved by a microbicide. In such skin-surface and skin-penetrating applications, the esterases produced by the micro-organism hydrolyse a portion of the active ingredient and, in so doing, inhibit the action of the esterase and further growth of the micro-organism. After a period of time, the micro-organism may resume its metabolic activity and the above-mentioned process is repeated, and repetition will occur until the active ingredient is used up.
According to the present invention we have now found that phenvl or benzyl benzoates of the following general formula (I)
Figure imgf000007_0001
wherein R represents a hydrogen or halogen atom or a C Δ alkyl, methoxy, ethoxy or acyloxy group, p is 0 or 1, and x, y and z are each 0 or an integer of from 1 to 5, are particularly effective as inhibitors of esterase-producing micro-organisms.
Benzoates of the formula (I) are hydrolysed by esterases to produce three mononuclear benzene compounds which between them bear at least two hydroxyl substituents and two carboxyl substituents. (The hydrolysis of benzyl 4-benzoyloxybenzoate and phenyl 2-benzoyloxybenzoate are shown in Figs 1 and 2, respectively, of the accompany¬ ing drawings.) The hydrolysis products are thus highly active in performing the previously-mentioned anti¬ microbial and pH-lowering functions, but not to the extent of being bacteriocidal as are most conventional deodorants: not only is the elimination of cutaneous flora medically undesirable, but the use of some conven¬ tional deodorants has caused adverse reactions. Moreover, the benzoates (I) afford the further advantages of being completely odourless and non-irritant.
Preferred benzoates (I) are those in which p equals 0 or 1; and x, y and z are each zero. Such com¬ pounds have the advantage of being easy to manufacture from cheap starting materials, although the 4-benzoyloxy- benzoates are preferred from the point of view of easy purification, being solids and therefore easy to crystal¬ lize. Such unsubstituted benzoates (I) have the further advantage of being generally more soluble than compounds having substituted nuclei.
Although the presence of hydroxyl substituents on the nuclei of the parent molecule increases its solu¬ bility in water, such hydroxyl substitution can lead to increased toxic effects, and is therefore generally less preferred: and although the presence of halogen substituents increases the activity of the hydrolysis products, such halogen substitution can again lead to increased toxic effects and is also less preferred. As the 2-benzoyloxybenzoates of the general formula (I) yield a salicylic acid among their hydrolysis pro¬ ducts, which can have an irritant effect, and the presence of a group at the 2-position can give rise to instability because of steric hindrance, and as the 3-benzoyloxy- benzoates are more expensive to produce, the 4-benzoyloxy- benzoates are generally preferred.
The primary use of benzoates (I) is as the active ingredient in a personal deodorant composition. For such an application the benzoate is first dissolved in, preferably, a perfume to form a perfume concentrate containing 5% to 50%, preferably say 10% benzoate, which is then added in an amount of about 1% to 2% to a suitable vehicle, for example ethyl alcohol, to form a deodorant composition in which the active ingredient is present in an amount of 0.1% to 0.2% and which is suitable for application by aerosol or mechanical spray.
A further use of the benzoates (1) is in the treatment of dandruff and acne where decomposition of the skin fats causes irritation. To prepare a skin lotion, for the treatment of acne, between 0.5% and 20%, and preferably about 5%, of active ingredient is incorporated in a vehicle which may be composed of di¬ methyl sulphoxide, polyol, ethanol and water in suitable proportions. Anti-inflammatory substances such as hydros- cortisone or glycyrrhetic acid and healing agents such as allantoin, may also be incorporated in the end product.
As a scalp lotion for the treatment of dandruff, active ingredient within the above percentages is incor¬ porated in a hydro-alcoholic vehicle, using solubilising agents as necessary.
As a powder for the treatment of tinea pedis and foot odour, active ingredient (if liquid) , within the above percentages, is adsorbed onto amorphous silica powder or light magnesium carbonate which is then mixed with say 50% talcum, starch or other- suitable powder. If the active ingredient is solid, usually crystalline, the crystals are finely ground, for example in a micron- iser, and then mixed with say 50% talcum, starch or other suitable powder.
Suitable perfume compositions may also be incor¬ porated in the scalp/skin lotions and foot powders.
The skin and scalp lotions may be supplied in sprinkler bottles for application to the scalp or the affected skin area in the form of liquid droplets which are massaged into the scalp/skin. Alternatively, the lotion may be applied by means of a pad or compress which is pre-impregnated and supplied in a sealed package'; the pad is partially exposed and then applied to an affected skin area, at least once per day. In further alternative forms, the inhibitors for use in treating the scalp or skin may comprise ointments, gels, creams, lotions , sprays or powders .
The inhibitors for foot treatment are preferably in powder form, as indicated above, but might also be supplied as liquids or in sprays etc.
An example of the preparation of what is believed to be the most soluble and active ingredient for use in the above compositions will now be described.
EXAMPLE Preparation of Benzyl - 4-benzoyloxybenzoate 0.5 mol (114 g) - of benzyl 4-hydroxybenzoate was dissolved in 500 mol of 5% sodium hydroxide solution.
0.51 mol (72 g) of benzoyl chloride was then added with rapid stirring. The reaction began almost: immediately accompanied by a rise in temperature. The reaction was completed in about 30 minutes when the odour of benzoyl chloride had disappeared and benzyl 4-benzoyloxybenzoate had precipitated as a fine powder or dense oil. The reaction mixture was then cooled and the aqueous liquid decanted. The reaction product was washed with water until the washings were neutral, and then filtered. Finally the crude product was recrystallized from hot 80% ethanol.
The reaction scheme may be represented as follows:
Figure imgf000012_0001
It will be appreciated that all the substituted products may be prepared by this general method.

Claims

CLAIMS :
1. A deodorant composition comprising, as active ingredient, an aromatic benzoate of the following general formula (I) :
Figure imgf000013_0001
wherein R represents a hydrogen or halogen atom or a C, 4 alkyl, methoxy, ethoxy or acyloxy group, p is 0 or 1, and x, y and z are each 0 or an integer of from 1 to 5, and a vehicle.
2. A dermatological composition comprising as active ingredient an aromatic benzoate of the general formula
(I) :
Figure imgf000013_0002
wherein R represents a hydrogen or halogen atom or a C, . alkyl, methoxy, ethoxy or acyloxy group, p is 0 or 1, and x, y and z are each O or an integer of from 1 to 5, and a vehicle.
3. A composition as claimed in claim 1 or 2 an'd additionally comprising a perfume composition.
4. A composition as claimed in claim 1, 2 or 3 wherein the aromatic benzoate is of the general formula (I) in which p = 0 or 1.
5. A composition as claimed in any preceding claim wherein the aromatic benzoate of the general formula (I) is a 4-benzoyloxy-benzoate.
6. An aromatic benzoate for use as an inhibitor of esterase-producing micro-organisms, the benzoate of the following general formula (I):
Figure imgf000014_0001
wherein R represents hydrogen or halogen atom or a C, alkyl, methoxy, ethoxy or acyloxy group, p is 0 or 1, and x, y and z are each 0 or an integer of from 1 to 5.
7. A benzoate as claimed in claim 6 for use as a personal deodorant.
8. A benzoate as claimed in claim 6 for use as a dermatological agent.
9. Use as a personal deodorant of an aromatic benzo¬ ate of the following general formula (I) :
Figure imgf000015_0001
wherein R represents a hydrogen or halogen atom or a C._4 alkyl, methoxy, ethoxy or acyloxy group, p is 0 or 1, and x, y and z are each 0 or an integer of from 1 to 5.
10. Use in the manufacture of a medicament for treat¬ ing dermatological conditions of an aromatic benzoate of the following general formula (I) :
Figure imgf000016_0001
wherein R represents a hydrogen or halogen atom or a C, . alkyl, methoxy, ethoxy or acyloxy group, p is 0 or 1, and x, y and z are each 0 or an integer of from 1 to 5.
11. Use as claimed in claim 9 or 10 of an aromatic benzoate of the general formula (I) in which p = 0 or 1.
12. Use as claimed in claim 9 or 10 of an aromatic benzoate of general formula (I), being a 4-benzoyloxy¬ benzoate.
PCT/GB1990/001750 1989-11-15 1990-11-13 Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms WO1991007165A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP90916501A EP0606197B1 (en) 1989-11-15 1990-11-13 Use of aromatic benzoates as personal deodorants
DE69025206T DE69025206T2 (en) 1989-11-15 1990-11-13 USE OF AROMATIC BENZOATS AS DEODORANTS
US07/856,955 US5683682A (en) 1989-11-15 1990-11-13 Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898925833A GB8925833D0 (en) 1989-11-15 1989-11-15 Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms
GB8925833.9 1989-11-15

Publications (1)

Publication Number Publication Date
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EP (1) EP0606197B1 (en)
JP (1) JPH05501881A (en)
AT (1) ATE133557T1 (en)
AU (1) AU6646590A (en)
DE (1) DE69025206T2 (en)
GB (1) GB8925833D0 (en)
WO (1) WO1991007165A1 (en)
ZA (1) ZA909124B (en)

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US5354737A (en) * 1993-08-13 1994-10-11 The Mennen Company Fragrance composition containing substantial amounts of acetyl hexamethyl tetralin, and deodorant composition containing the fragrance composition
US5380707A (en) * 1993-08-13 1995-01-10 The Mennen Company Enhanced efficacy, long-lasting fragrance composition, and deodorant composition, for masking malodor, containing the fragrance composition
WO1997016164A1 (en) * 1995-10-28 1997-05-09 Henkel Kommanditgesellschaft Auf Aktien Deodorizing preparations containing cationic biopolymers, aluminium hydrochlorate and esterase inhibitors
US5968488A (en) * 1996-10-21 1999-10-19 Henkel Kommanditgesellschaft Auf Aktien Deodorizing preparations containing cationic biopolymers, aluminum hydrochlorate and esterase inhibitors
US8685380B2 (en) 2010-10-25 2014-04-01 C.B. Fleet Company, Inc. Deodorant spray
US8802653B2 (en) 2010-10-01 2014-08-12 C.B. Fleet Company, Inc. Deodorant compositions
WO2015162392A1 (en) 2014-04-25 2015-10-29 Robertet S.A. Novel derivatives of benzyl benzoate

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GB9814732D0 (en) 1998-07-07 1998-09-02 Unilever Plc Method of reducing or preventing malodour
GB9814733D0 (en) 1998-07-07 1998-09-02 Unilever Plc Method of reducing or preventing malodour
NZ531890A (en) * 2002-02-28 2006-02-24 Japan Tobacco Inc Ester compound and medicinal use thereof
GB0217447D0 (en) * 2002-07-29 2002-09-04 Betts John A Personal deodorant
EP1669345A4 (en) * 2003-08-29 2008-02-20 Japan Tobacco Inc Ester derivative and medicinal use thereof
US20060030623A1 (en) * 2004-07-16 2006-02-09 Noboru Furukawa Agent for the treatment or prevention of diabetes, obesity or arteriosclerosis
US8101774B2 (en) * 2004-10-18 2012-01-24 Japan Tobacco Inc. Ester derivatives and medicinal use thereof
WO2006046623A1 (en) * 2004-10-25 2006-05-04 Japan Tobacco Inc. Solid medicinal preparation improved in solubility and stability and process for producing the same
WO2006078986A2 (en) * 2005-01-21 2006-07-27 Vertex Pharmaceuticals Incorporated Quorum sensing modulators
US20110150955A1 (en) 2009-12-23 2011-06-23 Shannon Elizabeth Klingman Products and Methods for Reducing Malodor from the Pudendum

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FR2108219A1 (en) * 1970-09-14 1972-05-19 Synvar Ass Limiting erythema of epidermis - by application of sunscreen cpd precursor
WO1985003289A1 (en) * 1984-01-25 1985-08-01 Yoshitomi Pharmaceutical Industries, Ltd. Parahydroxybenzoate compound
WO1987006827A1 (en) * 1986-05-13 1987-11-19 Robertet S.A. Inhibitors of esterase-producing micro-organisms, for use primarily in dermatology and cosmetics

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EP0606197A1 (en) 1994-07-20
JPH05501881A (en) 1993-04-08
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ATE133557T1 (en) 1996-02-15
US5683682A (en) 1997-11-04
GB8925833D0 (en) 1990-01-04
DE69025206D1 (en) 1996-03-14
EP0606197B1 (en) 1996-01-31
AU6646590A (en) 1991-06-13
ZA909124B (en) 1991-09-25

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